Tumblr will make Yahoo as cool as that Hot Topic shirt made you in 6th grade

Several sources have reported that Yahoo wants to buy Tumblr for $1 billion. That’s an awfully high number, but I can see why Tumblr would take a billion dollar buyout from Yahoo. First of all, that’s Beyonce money. And Tumblr is struggling to monetize, as its scramble for native mobile ads shows. Also … there is no second of all, because Yahoo is going to do absolutely nothing else for the long-term benefit of Tumblr. Now, one may argue that Yahoo doesn’t need to do anything else for Tumblr since they’d give them a whack of cash, and that the cool kid vibe of Tumblr would inarguably help the stodginess that continues to follow Yahoo around, even post Marissa Mayer hiring. But if you like using Tumblr, there are two scenarios that will arise from a Yahoo buyout, and neither of them look good.

Scenario one: Yahoo destroys Tumblr and takes its tech

This is the worst-case scenario. Yahoo is a hot, hot mess, and even though recent changes have been savvy, it could infect Tumblr with its some of its former self to a point where Tumblr loses all its followers and falls into a Friendster-esque state of Internet ghost town disarray. Am I being unfair to Yahoo? Nah. Marissa Mayer is a bawse but the company is still troubled. Let’s review: what was one of the most recent things Yahoo bought? Ah yes – Summly. Yahoo paid a British teen $30 million for his app, which summarizes news articles, and then shut it down to incorporate the technology into its own services. Yahoo could go the Summly route with Tumblr and buy it out only to shut it down and merge it into the Yahoo Stew of Failure.

But it’s not very likely that Yahoo would risk alienating Tumblr’s userbase by completely getting rid of everything that makes it uniquely Tumblr-y, so a shut-down seems improbable. Summly is one thing and Tumblr is so, so another. So even though it’s not going to be good for Tumblr, Yahoo probably isn’t going to dismember and defile the service beyond the point of recognition. Which leads me to scenario #2…

Scenario two: Yahoo gradually makes Tumblr worse

This scenario is much more likely. Yahoo is making some major progress with Mayer behind the helm, with an attractive new mail app, a snazzy homepage redesign, and plenty of interesting (but far more low-profile) acquisitions. It has a big problem though – it’s simply not cool. It’s the Miracle Whip of the Internet. Some old people use it because they don’t know any better, but it’s an antiquated, fuddy-duddy brand – and attempts at catching up with its competitors, like adding Dropbox to its mail service, are decent progress but still leave the company trailing behind. In a survey I just conducted featuring myself and my friend Zach, even Bing is cooler than Yahoo. That Outlook mail client is slick …

Yahoo is a decrepit succubus that wants to leech off the coolness of Tumblr. But it’s not worth $1 billion to simply buy Tumblr, let it run exactly as it has been, and hope that the fact that Yahoo owns Tumblr will imbue it with some kind of street cred. No, Yahoo will almost certainly want to integrate Tumblr into its services, to encourage the coveted “hip” demographic to wander onto Yahoo content. Might I reference Flickr: The Internet’s beloved photo service has recently reclaimed its spot among the greats, but Yahoo did fumble that buy out for awhile and users were jumping ship and angry at the changes.

Now, Tumblr is “looking for a liquidity event,” according to one of Adweek’s sources. They have their mind on their money and their money on their mind. Tumblr kills it on the user side of things but it’s been having problems monetizing and Yahoo could help it out on that end. But I have a feeling any major grab for monetization via Yahoo’s advertising team will seriously mess with the things that make Tumblr so great. It’s not a good situation because Tumblr’s investors and board want it to make more money, but making a deal with Yahoo is like making a deal with the world’s least-hip devil. Not Al Pacino in Devil’s Advocate. More like Adam Sandler in Little Nicky. The help from the advertising side will come at a price, and that price will be mucking up Tumblr’s user experience.

Scenario three: What, a third scenario? Yep – and it involves Facebook and also, still the ruination of Tumblr

Of course, this deal is far from inked. And now that the acquisition cat is out of the rumor bag, Yahoo might have some competition to win Tumblr’s soul.

Facebook is trying to remain cool while simultaneously becoming ever-more obnoxious as an ad platform, so it may be interested in Tumblr as a way to bulk up its appeal for younger users, who increasingly choose other social mediums. And if the Instagram buyout is any indication, Zuckerberg doesn’t exactly shy away from quick-fire major purchases of “cool” platforms. GigaOM speculated that a Facebook last-minute sneaky buyout could happen, especially considering how Tumblr CEO David Karp likes to play nice with the social network.

Facebook would probably be marginally less soul-sucking than Yahoo if it bought Tumblr, but emphasis on the marginally. Look, I get it: Companies need to make money. But when it comes to social media, you have to straddle a really fine line between finding ways to profit and keeping your service an enjoyable experience for users – and they can smell the stink of money-grabs from a mile away – and as of late, Facebook has been as worse at walking that line than a liquored up Reese Witherspoon.

Yahoo (and in my realistic hypothetical, Facebook) is interested in Tumblr because it is cool. But it’s only cool because it offers a purer user experience than a monetization-oriented service can. It might be able to eke out a path that lets it boost profit without creeping users out, but if Yahoo (or Facebook) gets put in charge of carving that route, my guess is the collateral damage will be too much, and the valuable 18-to-24 set will migrate.

Chasing hipness is a futile task. But Tumblr has it. Will it trade being a beloved social network for being a wealthy one? Probably, but it’s going to decrease its shelf-life.

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